Three-Dimensional Structures of 3/4/5-O-feruloylquinic Acids by NMR Spectroscopy and Quantum Chemistry Calculation

doi:10.11938/cjmr20243115

Abstract

Abstract:

3/4/5-O-feruloylquinic acids (3/4/5-O-FQA) have antioxidant activity, which is beneficial to disease prevention and human health maintenance, however, their exact 3D structures are still unknown. In the present work, the structures of 3/4/5-O-FQA in gas phase, D₂O solution and DMSO-d₆ solution are investigated respectively using ¹H nuclear magnetic resonance (NMR) spectroscopy combined with quantum chemistry calculation. We observed a difference of 4.147° in dihedral angle τ (H3C3O1C9) on the esterification site H-3 for 3-O-FQA in D₂O and DMSO-d₆ solutions, which can explain the difference on ¹H NMR spectra for H-3 atom of 3-O-FQA in the two solutions. This work presents the 3D structures of 3/4/5-O-FQA, offering valuable insights for further studies on their properties and potential applications.

Key words: 3D structure, NMR, quantum chemistry calculation, chemical shift, 3/4/5-O-feruloylquinic acid

CLC Number:

O482.53

ZHANG Jiayu, NIE Wenbo, TU Zhao, ZHENG Limin, WANG Yan, YANG Chunsheng. Three-Dimensional Structures of 3/4/5-O-feruloylquinic Acids by NMR Spectroscopy and Quantum Chemistry Calculation[J]. Chinese Journal of Magnetic Resonance, 2025, 42(1): 47-55.

Figures/Tables 10

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3-O-FQA		4-O-FQA		5-O-FQA
H₂O	DMSO	H₂O	DMSO	H₂O	DMSO
	12.47	1.93	15.38	15.19	12.58	12.85
	19.67	14.71	22.19	22.14	15.50	16.12
	31.81	29.02	25.61	25.43	29.57	30.10
	38.61	32.85	34.29	34.24	40.51	40.80
	53.25	50.29	54.94	55.32	44.85	45.36
	62.17	61.66	58.46	58.30	57.94	58.49
	72.09	71.09	64.52	64.65	69.16	69.59
	87.96	86.18	81.22	81.66	84.51	84.74
	89.33	89.63	118.58	118.16	102.86	102.94
	123.20	123.03	127.79	127.73	114.08	114.54

Method	¹H NMR												RMSD
Method	δ_H-2	δ_H-2’	δ_H-3	δ_H-4	δ_H-5	δ_H-6	δ_H-6’	δ_H’-2	δ_H’-5	δ_H’-6	δ_H’-7	δ_H’-8	RMSD
B972/ pcSseg-1	2.41	2.19	5.28	3.68	3.79	2.17	2.17	8.08	7.24	7.52	7.88	6.61	0.34
B3LYP/ 6-311++g(d,p)	2.33	2.26	5.30	3.90	3.91	2.37	2.30	8.14	7.16	7.52	8.17	6.79	0.39
revTPSS/ pcSseg-1	2.46	2.26	5.32	3.81	3.85	2.29	2.25	7.82	7.02	7.29	7.60	6.39	0.24
EXP^a	2.13	2.11	5.31	3.67	4.08	2.20	1.95	7.23	6.82	7.12	7.61	6.41

	3-O-FQA		4-O-FQA		5-O-FQA
	D₂O	DMSO-d₆	D₂O	DMSO-d₆	D₂O	DMSO-d₆
δ_H-3	5.25 (5.28)	5.34 (5.42)	4.21 (4.21)	3.71 (4.21)	4.14 (4.23)	3.99 (4.23)
δ_H-4	3.61 (3.68 )	3.67 (3.68)	4.77 (4.90)	4.79 (4.90)	3.75 (3.67)	3.48 (3.67)
δ_H-5	4.02 (3.79)	3.62 (3.78)	4.16 (3.90)	4.17 (3.90)	5.18 (5.39)	5.19 (5.40)
RMSD	0.13	0.10	0.17	0.33	0.13	0.21